Triethylamine → (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 440095

Reaction equation

HRID 440095 reaction equation
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C>CS(C)=O.C[C@@H]1[C@@H]2C(=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@H]2O)C(=O)C2C(O)=CC=CC1=2.OP(=O)=O.OP(=O)=O.OP(=O)=O.[O-]P(=O)=O.[Na+]>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

Product 1

HCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 178461157HCID 178461157, compoundSolvent

Procedure

To a stirred solution of N-Cbz-L-prolinol (5g, 21.26 mmol, from steps 24b or 24c above) in 20 mL of anhydrous DMSO were added 8.89 mL (63.79 mmol) of triethylamine and 10.75 g (63.79 mmol) of SO3 -pyridine complex in 35 mL of DMSC). The reaction mixture was stirred at room temperature for 10 min, then poured into 200 mL of ice water. The mixture was extracted with ether, the extract was dried over Na2SO4 and concentrated to afford the title product, 3.058 g (70% yield).

Workup

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe extract was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6be8340291294a508f77f2e7a867908c
Source dataset
uspto-grants-1996_05
Patent number
US05516912

Linked notes

Loading…